potassium carbonate; sodium iodide in acetone 6 h; Reflux;

1: sulfuric acid / 120 - 125 °C 2: potassium carbonate; sodium iodide / acetone / Reflux View Scheme

1: sulfuric acid / 4 h / 25 - 125 °C 2: potassium carbonate; sodium iodide / acetone / 2 h / 25 - 60 °C View Scheme

1: sulfuric acid / 120 - 125 °C 2: potassium carbonate; sodium iodide / acetone / Reflux View Scheme

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 2 h / 0 - 5 °C 3.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C 5.1: (2S,3S)-2,3-dihydroxybutanedioic acid / isopropyl alcohol / 16 h / 30 - 35 °C 5.2: 10 - 15 °C 6.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave 7.1: hydrogen / 5 palladium on charcoal / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave View Scheme

1.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 1.2: 3 h / 10 °C 2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C View Scheme

1.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 1.2: 3 h / 10 °C 2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 3.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 4.1: isopropyl alcohol / 15 h / 25 - 86 °C 5.1: sodium hydroxide / water 6.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 6.2: 1 h / -65 - -60 °C 7.1: thionyl chloride / 10 °C / Reflux 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 9.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C View Scheme

1.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 1.2: 3 h / 10 °C 2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 3.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 4.1: isopropyl alcohol / 15 h / 25 - 86 °C 5.1: sodium hydroxide / water 6.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 6.2: 1 h / -65 - -60 °C 7.1: thionyl chloride / 10 °C / Reflux 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 25 - 30 °C 9.1: hydrogen / 5 Pd(II)/C(eggshell) / methanol / 50 - 55 °C 10.1: dichloromethane / 1.5 h / 0 - 5 °C 10.2: 1 h / 0 - 5 °C View Scheme

1.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 1.2: 3 h / 10 °C 2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 3.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 4.1: isopropyl alcohol / 15 h / 25 - 86 °C 5.1: sodium hydroxide / water 6.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 6.2: 1 h / -65 - -60 °C 7.1: thionyl chloride / 10 °C / Reflux View Scheme

1.1: sodium tetrahydroborate / ethylene glycol dimethyl ether / 0.17 h 1.2: 3 h / 10 °C 2.1: triethylamine / dichloromethane / 12 h / 25 - 30 °C 3.1: acetonitrile / 30 h / 95 - 100 °C / autoclave; Sealed tube 4.1: isopropyl alcohol / 15 h / 25 - 86 °C 5.1: sodium hydroxide / water 6.1: ethyl bromide; iodine; magnesium / tetrahydrofuran / 1 h / 55 °C / Reflux 6.2: 1 h / -65 - -60 °C View Scheme